Record Information
Version2.0
Created at2022-03-17 20:31:29 UTC
Updated at2022-03-17 20:31:29 UTC
NP-MRD IDNP0046906
Secondary Accession NumbersNone
Natural Product Identification
Common NameViolanthin
Description Violanthin is found in Adenia mannii, Angiopteris hypoleuca, Ephedra torreyana, Glycyrrhiza inflata and Viola arvensis . Violanthin was first documented in 1998 (PMID: 9548860).
Structure
Thumb
SynonymsNot Available
Chemical FormulaC27H30O14
Average Mass578.5187 Da
Monoisotopic Mass578.16356 Da
IUPAC Name5,7-dihydroxy-2-(4-hydroxyphenyl)-6-[(2S,3R,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]-8-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]-4H-chromen-4-one
Traditional Nameviolanthin
CAS Registry Number40581-17-7
SMILES
C[C@@H]1O[C@H]([C@H](O)[C@H](O)[C@H]1O)C1=C(O)C([C@@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)=C(O)C2=C1OC(=CC2=O)C1=CC=C(O)C=C1
InChI Identifier
InChI=1S/C27H30O14/c1-8-17(31)21(35)23(37)27(39-8)16-20(34)15(26-24(38)22(36)18(32)13(7-28)41-26)19(33)14-11(30)6-12(40-25(14)16)9-2-4-10(29)5-3-9/h2-6,8,13,17-18,21-24,26-29,31-38H,7H2,1H3/t8-,13+,17-,18+,21+,22-,23+,24+,26-,27-/m0/s1
InChI KeyMVOUGOXRXQDXDC-RSPRXDBDSA-N
Experimental Spectra
Not Available
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Adenia manniiLOTUS Database
Angiopteris hypoleucaLOTUS Database
Ephedra torreyanaLOTUS Database
Glycyrrhiza inflataLOTUS Database
Oryza sativaFooDB
Viola arvensisPlant
Chemical Taxonomy
Description Belongs to the class of organic compounds known as flavonoid 8-c-glycosides. Flavonoid 8-C-glycosides are compounds containing a carbohydrate moiety which is C-glycosidically linked to 8-position of a 2-phenylchromen-4-one flavonoid backbone.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassFlavonoids
Sub ClassFlavonoid glycosides
Direct ParentFlavonoid 8-C-glycosides
Alternative Parents
Substituents
  • Flavonoid-8-c-glycoside
  • 4'-hydroxyflavonoid
  • 5-hydroxyflavonoid
  • 7-hydroxyflavonoid
  • Flavone
  • Hydroxyflavonoid
  • Phenolic glycoside
  • C-glycosyl compound
  • Chromone
  • Glycosyl compound
  • Benzopyran
  • 1-benzopyran
  • 1-hydroxy-2-unsubstituted benzenoid
  • Phenol
  • Pyranone
  • Pyran
  • Monocyclic benzene moiety
  • Oxane
  • Monosaccharide
  • Benzenoid
  • Heteroaromatic compound
  • Vinylogous acid
  • Secondary alcohol
  • Polyol
  • Oxacycle
  • Dialkyl ether
  • Ether
  • Organoheterocyclic compound
  • Hydrocarbon derivative
  • Organic oxygen compound
  • Organooxygen compound
  • Primary alcohol
  • Organic oxide
  • Alcohol
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP-0.46ALOGPS
logP-1.8ChemAxon
logS-2ALOGPS
pKa (Strongest Acidic)5.76ChemAxon
pKa (Strongest Basic)-3.6ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count14ChemAxon
Hydrogen Donor Count10ChemAxon
Polar Surface Area247.06 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity137.61 m³·mol⁻¹ChemAxon
Polarizability55.21 ųChemAxon
Number of Rings5ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB006428
KNApSAcK IDC00006230
Chemspider IDNot Available
KEGG Compound IDC10196
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem CompoundNot Available
PDB IDNot Available
ChEBI ID9992
Good Scents IDNot Available
References
General References
  1. Fraisse D, Carnat A, Carnat AP, Texier O, Elias R, Balansard G, Lamaison JL: [Principal constituents from flowering aerial parts of wild pansy]. Ann Pharm Fr. 2001 Apr;59(2):119-24. [PubMed:11320336 ]
  2. Dung HV, Cuong TD, Chinh NM, Quyen D, Kim JA, Byeon JS, Woo MH, Choi JS, Min BS: Compounds from the aerial parts of Piper bavinum and their anti-cholinesterase activity. Arch Pharm Res. 2015;38(5):677-82. doi: 10.1007/s12272-014-0432-3. Epub 2014 Jul 9. [PubMed:25005067 ]
  3. Carnat AP, Carnat A, Fraisse D, Lamaison JL, Heitz A, Wylde R, Teulade JC: Violarvensin, a new flavone di-C-glycoside from Viola arvensis. J Nat Prod. 1998 Feb;61(2):272-4. doi: 10.1021/np9701485. [PubMed:9548860 ]